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ChemicalBook CAS DataBase List 2-Nitrodiphenylamine

2-Nitrodiphenylamine synthesis

14synthesis methods
The synthesis of 2-Nitrodiphenylamine is as follows:The mixture of phenylboronic acid (1 mmol), aromatic amine (1.2 mmol) and 0.12 g (2 mmol) of KF in DMSO (4 mL) were added to Cu-IS-AMBA-MNPs (0.06 g, 0.025 mmol) at 130 °C under nitrogen atmosphere for 2 h with vigorous stirring. Then, after completion of the reaction, the catalyst was separated by an external magnet and washed with dry CH2Cl2 three times and checked for its reusability. The solvent of the reaction mixture was evaporated by a rotary evaporator and then ethyl acetate and water were added to the residue. The organic layer was dried over anhydrous MgSO4. The solvent was evaporated under reduced pressure and the crude product was purified by column chromatography using ethyl acetate/n-hexane.

synthesis of 2-Nitrodiphenylamine.png
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Yield:119-75-5 98%

Reaction Conditions:

with potassium fluoride in dimethyl sulfoxide at 130; for 2 h;Inert atmosphere;Ullmann-Goldberg Substitution;

Steps:

General procedure for N-arylation reactions

General procedure: The mixture of phenylboronic acid (1 mmol), aromatic amine (1.2 mmol) and 0.12 g (2 mmol) of KF in DMSO (4 mL) were added to Cu-IS-AMBA-MNPs (0.06 g, 0.025 mmol) at 130 °C under nitrogen atmosphere for 2 h with vigorous stirring. Then, after completion of the reaction, the catalyst was separated by an external magnet and washed with dry CH2Cl2 three times and checked for its reusability. The solvent of the reaction mixture was evaporated by a rotary evaporator and then ethyl acetate and water were added to the residue. The organic layer was dried over anhydrous MgSO4. The solvent was evaporated under reduced pressure and the crude product was purified by column chromatography using ethyl acetate/n-hexane.

References:

Khodaei, Mohammad Mehdi;Alizadeh, Abdolhamid;Haghipour, Maryam [Research on Chemical Intermediates,2019,vol. 45,# 5,p. 2727 - 2747]

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